Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO                         2                          and H                         2

Zhengang Ke; Zhenzhen Yang; Zhenghui Liu; Bo Yu; Yanfei Zhao; Shien Guo; Yunyan Wu; Zhimin Liu

doi:10.1021/acs.orglett.8b02384

Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂

Zhengang Ke, Zhenzhen Yang, Zhenghui Liu, Bo Yu, Yanfei Zhao, Shien Guo, Yunyan Wu, Zhimin Liu

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

Herein, a novel route to synthesize unsymmetrically N,N-disubstituted formamides is reported, which is achieved via reductive coupling of primary amine and aldehyde with CO ₂ /H ₂ over a cobalt-based catalytic system composed of CoF ₂ , P(CH ₂ CH ₂ PPh ₂ ) ₃ and K ₂ CO ₃ . The mechanism investigation indicates that a secondary amine is formed via hydrogenation of the imine originated from aldehyde and primary amine, which further reacts with HCOOH generated from CO ₂ hydrogenation, resulting in the formation of NNFA finally.

Original language	English
Pages (from-to)	6622-6626
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.8b02384
State	Published - Nov 2 2018
Externally published	Yes

Funding

This work was financially supported by the National Natural Science Foundation of China (Grant No. 21533011), and Chinese Academy of Sciences (Grant No. QYZDY-SSW-SLH013).

Funders	Funder number
National Natural Science Foundation of China	21533011
Chinese Academy of Sciences	QYZDY-SSW-SLH013

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.orglett.8b02384

Cite this

Ke, Z., Yang, Z., Liu, Z., Yu, B., Zhao, Y., Guo, S., Wu, Y., & Liu, Z. (2018). Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ Organic Letters, 20(21), 6622-6626. https://doi.org/10.1021/acs.orglett.8b02384

Ke, Zhengang ; Yang, Zhenzhen ; Liu, Zhenghui et al. / Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ In: Organic Letters. 2018 ; Vol. 20, No. 21. pp. 6622-6626.

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title = " Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO 2 and H 2 ",

abstract = " Herein, a novel route to synthesize unsymmetrically N,N-disubstituted formamides is reported, which is achieved via reductive coupling of primary amine and aldehyde with CO 2 /H 2 over a cobalt-based catalytic system composed of CoF 2 , P(CH 2 CH 2 PPh 2 ) 3 and K 2 CO 3 . The mechanism investigation indicates that a secondary amine is formed via hydrogenation of the imine originated from aldehyde and primary amine, which further reacts with HCOOH generated from CO 2 hydrogenation, resulting in the formation of NNFA finally.",

author = "Zhengang Ke and Zhenzhen Yang and Zhenghui Liu and Bo Yu and Yanfei Zhao and Shien Guo and Yunyan Wu and Zhimin Liu",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b02384",

language = "English",

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Ke, Z, Yang, Z, Liu, Z, Yu, B, Zhao, Y, Guo, S, Wu, Y & Liu, Z 2018, ' Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ ', Organic Letters, vol. 20, no. 21, pp. 6622-6626. https://doi.org/10.1021/acs.orglett.8b02384

Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ . / Ke, Zhengang; Yang, Zhenzhen; Liu, Zhenghui et al.
In: Organic Letters, Vol. 20, No. 21, 02.11.2018, p. 6622-6626.

Research output: Contribution to journal › Article › peer-review

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T1 - Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO 2 and H 2

AU - Ke, Zhengang

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AU - Yu, Bo

AU - Zhao, Yanfei

AU - Guo, Shien

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AU - Liu, Zhimin

PY - 2018/11/2

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AB - Herein, a novel route to synthesize unsymmetrically N,N-disubstituted formamides is reported, which is achieved via reductive coupling of primary amine and aldehyde with CO 2 /H 2 over a cobalt-based catalytic system composed of CoF 2 , P(CH 2 CH 2 PPh 2 ) 3 and K 2 CO 3 . The mechanism investigation indicates that a secondary amine is formed via hydrogenation of the imine originated from aldehyde and primary amine, which further reacts with HCOOH generated from CO 2 hydrogenation, resulting in the formation of NNFA finally.

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Ke Z, Yang Z, Liu Z, Yu B, Zhao Y, Guo S et al. Cobalt-Catalyzed Synthesis of Unsymmetrically N, N-Disubstituted Formamides via Reductive Coupling of Primary Amines and Aldehydes with CO ₂ and H ₂ Organic Letters. 2018 Nov 2;20(21):6622-6626. doi: 10.1021/acs.orglett.8b02384